CAROTENOLS AND OXYf'AT^OTENOT.R OF THE C40 SERIES 505 



zeaxanthin mono-cpoxidc and zoaxanthin di-cpoxide, depending upon 

 whether one or both /3-ionone rings are attacked. ^^^ 



Zeaxanthin mono-epoxide was found by Karrer et al.^^^ to be identical with 

 antheraxanthin; the latter compound is a carotenoid which was isolated by 

 Karrer and Oswald'"^ from the stamens of the tiger lily {Lilrum tigrinum). 



H3C CHj HjC CH3 



p CHi CH3 CHj CH3 Q 



/\ hhIhhhIhhhhIhhhIhh /\ 

 HjC C'C:C-C:C-C:C'C:C-C:C'C:C-C:C-C:C'C:C-C CH? 



H.I |> II l/H 



c c c c 



"^ C CH, HjC C 



H? H? 



Aiitheraxantliiii (zeaxanthin mono-epoxide) 



(d) Mutatoxanthin, C40H56O3. In the presence of halogen acids or chloro- 

 form, zeaxanthin mono-epoxide undergoes transformation similar to that of 

 the lutein epoxides. Thus, the epoxide is converted to a product with an 



Table 5 

 Comparison of Propertiks of Antheraxanthin (Zeaxanthin Mono-epoxide) and 



Mutatoxanthin" 



Property Antheraxanthin Mutatoxanthin 



Empirical formula C40H56O3 C4oH660:i 



Number ot double bonds 10 10 



Number of conjugated double bonds. 10 9 



Number of hj'droxyl groups 2 2 



Number of ether-bound oxj'gens 1 1 



Melting point, °C 205° 177° 



Position in chromatogram Upper Lower 



Absorption maxima (CS2), ni/x 510, 475 488, 459, 431 



Al)sorption maxima (C.HsOH), mn. . 479, 449 457, 427 



Reaction with cone. aq. HCl Blue, fading rapidly Blue, fading rapidly 



« P. Karrer and E. Jucker, Helv. Chim. Acta, 28, 300-315 (1945), p. 310. 



absorption maximum 23 m/x lower. The compound so prepared was 

 demonstrated by Karrer and Jucker^ ^^ to be identical with the so-called 

 mutatoxanthin which had been prepared earlier from violaxanthin.^^^ 



H,C CHj 



A _H "\ /"^ 



H2C C CCH3 CH3 CH3 CH3 r\ 



H\| I IIhhhIhhhhIhhhIhh /\ 



C HC-C:C-c:C'C:c-C:G-C:C-C:C-C:C-C:C-C CH? 



H0/\/\\0/ II l/H 



H3C C °" 



H2 



Mutatoxanthin 

 3« P. Karrer and A. Oswal.l, Helv. CMvi. Ada, 18, 1303-1305 (1935). 



